Synthesis and structure of helical supramolecular arrays

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 285-286

  Kawamoto, Tatsuya ^a   Hammes, Brian S ^a   Haggerty, Brian ^b   Yap, Glenn P A ^b   Rheingold, Arnold L ^b   Borovik, A S ^a  

^a KANSAS STATE UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001329163     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953227g     Document Type: Article

References (38)

1. General references: (a) Desiraju, G. D. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989. (b) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1304. (c) Transition Metals in Supramolecular Chemistry; Fabbrizzi, L., Poggi, A., Eds., Kluwer Academic: Dordrecht. 1994.
2. General references: (a) Desiraju, G. D. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989. (b) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1304. (c) Transition Metals in Supramolecular Chemistry; Fabbrizzi, L., Poggi, A., Eds., Kluwer Academic: Dordrecht. 1994.
3. General references: (a) Desiraju, G. D. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989. (b) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1304. (c) Transition Metals in Supramolecular Chemistry; Fabbrizzi, L., Poggi, A., Eds., Kluwer Academic: Dordrecht. 1994.
4. Kawamoto, T.; Prakash, O.; Ostrander, R.; Rheingold, A. L.; Borovik, A. S. Inorg. Chem. 1995, 34, 4294.
5. Most previously reported supramolecular metallohelices are racemates: (a) Lehn, J.-M., Rigault, A., Siegel, J.; Harrowfield, J.; Chevier, B.; Moras, D. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 2565. (b) Dietrich-Buchecker, C. O.; Sauvage, J.-M. Angew. Chem., Int. Ed. Engl. 1989, 28, 189. (c) Piguet, C.; Bernardinelli, G.; Bocquet, B.; Quattropani, A.; Williams, A. F. J. Am. Chem. Soc. 1992, 114, 7440. (d) Constable, E. D. Tetrahedron 1992, 48, 10013 and references therein. (e) Potts, K. T.; Keshavarz-K. M.; Tham, F. S.; Abruña, H D.; Arana, C. Inorg. Chem. 1993, 32, 4436.
6. Most previously reported supramolecular metallohelices are racemates: (a) Lehn, J.-M., Rigault, A., Siegel, J.; Harrowfield, J.; Chevier, B.; Moras, D. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 2565. (b) Dietrich-Buchecker, C. O.; Sauvage, J.-M. Angew. Chem., Int. Ed. Engl. 1989, 28, 189. (c) Piguet, C.; Bernardinelli, G.; Bocquet, B.; Quattropani, A.; Williams, A. F. J. Am. Chem. Soc. 1992, 114, 7440. (d) Constable, E. D. Tetrahedron 1992, 48, 10013 and references therein. (e) Potts, K. T.; Keshavarz-K. M.; Tham, F. S.; Abruña, H D.; Arana, C. Inorg. Chem. 1993, 32, 4436.
7. Most previously reported supramolecular metallohelices are racemates: (a) Lehn, J.-M., Rigault, A., Siegel, J.; Harrowfield, J.; Chevier, B.; Moras, D. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 2565. (b) Dietrich-Buchecker, C. O.; Sauvage, J.-M. Angew. Chem., Int. Ed. Engl. 1989, 28, 189. (c) Piguet, C.; Bernardinelli, G.; Bocquet, B.; Quattropani, A.; Williams, A. F. J. Am. Chem. Soc. 1992, 114, 7440. (d) Constable, E. D. Tetrahedron 1992, 48, 10013 and references therein. (e) Potts, K. T.; Keshavarz-K. M.; Tham, F. S.; Abruña, H D.; Arana, C. Inorg. Chem. 1993, 32, 4436.
8. Most previously reported supramolecular metallohelices are racemates: (a) Lehn, J.-M., Rigault, A., Siegel, J.; Harrowfield, J.; Chevier, B.; Moras, D. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 2565. (b) Dietrich-Buchecker, C. O.; Sauvage, J.-M. Angew. Chem., Int. Ed. Engl. 1989, 28, 189. (c) Piguet, C.; Bernardinelli, G.; Bocquet, B.; Quattropani, A.; Williams, A. F. J. Am. Chem. Soc. 1992, 114, 7440. (d) Constable, E. D. Tetrahedron 1992, 48, 10013 and references therein. (e) Potts, K. T.; Keshavarz-K. M.; Tham, F. S.; Abruña, H D.; Arana, C. Inorg. Chem. 1993, 32, 4436.
9. Most previously reported supramolecular metallohelices are racemates: (a) Lehn, J.-M., Rigault, A., Siegel, J.; Harrowfield, J.; Chevier, B.; Moras, D. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 2565. (b) Dietrich-Buchecker, C. O.; Sauvage, J.-M. Angew. Chem., Int. Ed. Engl. 1989, 28, 189. (c) Piguet, C.; Bernardinelli, G.; Bocquet, B.; Quattropani, A.; Williams, A. F. J. Am. Chem. Soc. 1992, 114, 7440. (d) Constable, E. D. Tetrahedron 1992, 48, 10013 and references therein. (e) Potts, K. T.; Keshavarz-K. M.; Tham, F. S.; Abruña, H D.; Arana, C. Inorg. Chem. 1993, 32, 4436.
10. Examples of chiral metallohelices: (a) Libman, J.; Tor, Y.; Shanzer, A. J. Am. Chem. Soc. 1987, 109, 5880. (b) Zarges, W.; Hall, J.; Lehn, J.-M.: Bolm, C. Helu. Chim. Acta 1991, 74, 1843. (c) Gilbert, A. M.; Katz. T. J.; Geiger, W. E.; Robben, M. P.; Rheingold, A. L. J. Am Chem. Soc. 1993, 115, 3199. (d) Suzuki, T.; Kotsuki, H.; Isobe, K.; Moriya, N.; Nakagawa. Y.; Ochi, M. Inorg. Chem. 1995, 34, 530. (e) Enemark, E. J.; Stack, T. D. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 996.
11. Examples of chiral metallohelices: (a) Libman, J.; Tor, Y.; Shanzer, A. J. Am. Chem. Soc. 1987, 109, 5880. (b) Zarges, W.; Hall, J.; Lehn, J.-M.: Bolm, C. Helu. Chim. Acta 1991, 74, 1843. (c) Gilbert, A. M.; Katz. T. J.; Geiger, W. E.; Robben, M. P.; Rheingold, A. L. J. Am Chem. Soc. 1993, 115, 3199. (d) Suzuki, T.; Kotsuki, H.; Isobe, K.; Moriya, N.; Nakagawa. Y.; Ochi, M. Inorg. Chem. 1995, 34, 530. (e) Enemark, E. J.; Stack, T. D. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 996.
12. Examples of chiral metallohelices: (a) Libman, J.; Tor, Y.; Shanzer, A. J. Am. Chem. Soc. 1987, 109, 5880. (b) Zarges, W.; Hall, J.; Lehn, J.-M.: Bolm, C. Helu. Chim. Acta 1991, 74, 1843. (c) Gilbert, A. M.; Katz. T. J.; Geiger, W. E.; Robben, M. P.; Rheingold, A. L. J. Am Chem. Soc. 1993, 115, 3199. (d) Suzuki, T.; Kotsuki, H.; Isobe, K.; Moriya, N.; Nakagawa. Y.; Ochi, M. Inorg. Chem. 1995, 34, 530. (e) Enemark, E. J.; Stack, T. D. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 996.
13. Examples of chiral metallohelices: (a) Libman, J.; Tor, Y.; Shanzer, A. J. Am. Chem. Soc. 1987, 109, 5880. (b) Zarges, W.; Hall, J.; Lehn, J.-M.: Bolm, C. Helu. Chim. Acta 1991, 74, 1843. (c) Gilbert, A. M.; Katz. T. J.; Geiger, W. E.; Robben, M. P.; Rheingold, A. L. J. Am Chem. Soc. 1993, 115, 3199. (d) Suzuki, T.; Kotsuki, H.; Isobe, K.; Moriya, N.; Nakagawa. Y.; Ochi, M. Inorg. Chem. 1995, 34, 530. (e) Enemark, E. J.; Stack, T. D. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 996.
14. Examples of chiral metallohelices: (a) Libman, J.; Tor, Y.; Shanzer, A. J. Am. Chem. Soc. 1987, 109, 5880. (b) Zarges, W.; Hall, J.; Lehn, J.-M.: Bolm, C. Helu. Chim. Acta 1991, 74, 1843. (c) Gilbert, A. M.; Katz. T. J.; Geiger, W. E.; Robben, M. P.; Rheingold, A. L. J. Am Chem. Soc. 1993, 115, 3199. (d) Suzuki, T.; Kotsuki, H.; Isobe, K.; Moriya, N.; Nakagawa. Y.; Ochi, M. Inorg. Chem. 1995, 34, 530. (e) Enemark, E. J.; Stack, T. D. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 996.
15. Reports of spontaneous resolution of metallohelices: (a) Scarrow, R. C.; White, D. L.; Raymond, K. N. J. Am. Chem. Soc. 1985, 107, 6541. (b) Dietrich-Buchecker, C. O.; Guilhem, J.; Pascard, C.; Sauvage, J.-P. Angew. Chem., Int. Ed. Engl. 1990, 29, 1154. (c) Kramer, R.; Lehn, J.-M.; Decian, A.; Fischer, J, Angew Chem., Int. Ed. Engl. 1993, 32, 703.
16. Reports of spontaneous resolution of metallohelices: (a) Scarrow, R. C.; White, D. L.; Raymond, K. N. J. Am. Chem. Soc. 1985, 107, 6541. (b) Dietrich-Buchecker, C. O.; Guilhem, J.; Pascard, C.; Sauvage, J.-P. Angew. Chem., Int. Ed. Engl. 1990, 29, 1154. (c) Kramer, R.; Lehn, J.-M.; Decian, A.; Fischer, J, Angew Chem., Int. Ed. Engl. 1993, 32, 703.
17. Reports of spontaneous resolution of metallohelices: (a) Scarrow, R. C.; White, D. L.; Raymond, K. N. J. Am. Chem. Soc. 1985, 107, 6541. (b) Dietrich-Buchecker, C. O.; Guilhem, J.; Pascard, C.; Sauvage, J.-P. Angew. Chem., Int. Ed. Engl. 1990, 29, 1154. (c) Kramer, R.; Lehn, J.-M.; Decian, A.; Fischer, J, Angew Chem., Int. Ed. Engl. 1993, 32, 703.
18. 21 has recently been reported: Hamuro, Y., Geib, S. J.; Hamilton, A. D. Angew, Chem., Int. Ed Engl. 1994, 33, 446.
19. Hammes, B. S.; Borovik, A. S. To be published.
20. M) 336 (20 300). 605 (264) nm. EPR (3.5-lutidine). g∥, 2.19 (A∥, 190 G), g⊥, 2.06.
21. 12, were confirmed by refinement of the η-parameter to 0.96(8) and 1.0(1), respectively. The structures were solved by directed methods, completed by subsequent difference Fourier syntheses, and refined by full-matrix least-squares procedures. Both structures lie on 2-fold axes. Non-carbon, non-hydrogen atoms were refined with anisotropic displacement coefficients. Carbon atoms were refined isotropically. Hydrogen atoms were treated as idealized contributions. Phenyl rings were refined as rigid bodies in Cu1(lut).
22. w) = 0.0519 (0.0579), GOF = 1.1.
23. 2I is a mixture of right- and left-handed helices which are in rapid exchange at room temperature.
24. Physical separation of the enantiomeric crystals and further characterization of their solid state properties are under investigation.
25. For Cu1(lut), two unique edge-on interactions are observed at centroid-centroid distances of 5.39 and 6.30 Å. Four weak methyl-aryl interactions between the methyl groups of the coordinated lutidine and the aromatic rings of neighboring helices are also observed at distances of 4.07 Å.
26. Additional lattice structural parameters for Cu1(py): (a) Each metallohelix has two additional edge-to-face interactions with helices in adjacent arrays, centroid-centroid distances are 5.74 and 6.35 Å. (b) Two Cu-Cu distances of 14.988(3) and 10.598(2) Å are observed between neighboring metallohelices within an array.
27. 16
28. (a) Burley, S. K., Petsko, G A. J. Am. Chem. Soc. 1986, 108, 7995.
29. (b) Burley, S. K.; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125.
30. (c) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
31. (d) Hunter, C. A. Chem. Soc. Rev. 1994, 101 and references therein.
32. (e) Hobza, P.; Selzle, H. L.; Schlag, E. W. J. Am. Chem. Soc. 1994, 116, 3500.
33. For examples of other systems that use edge-on aromatic interactions, see the following. (a) Protein secondary and tertiary structure: Burley, S. K.; Petsko, G. A. Science (Washington, D.C.) 1985, 229, 23. (b) Crystal lattices of aromatic molecules: Desiraju, G. R.; Gavezzotti, A. J. Chem. Soc., Chem. Commun. 1989. 621 and references therein. (c) To effect stereoselectivity in metal complexes: Karpishin, T. B.; Stack, T. D. P.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 6115. (d) In molecular recognition: Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561. Hunter, C. A. J. Chem. Soc., Chem. Commun. 1991, 749.
34. For examples of other systems that use edge-on aromatic interactions, see the following. (a) Protein secondary and tertiary structure: Burley, S. K.; Petsko, G. A. Science (Washington, D.C.) 1985, 229, 23. (b) Crystal lattices of aromatic molecules: Desiraju, G. R.; Gavezzotti, A. J. Chem. Soc., Chem. Commun. 1989. 621 and references therein. (c) To effect stereoselectivity in metal complexes: Karpishin, T. B.; Stack, T. D. P.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 6115. (d) In molecular recognition: Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561. Hunter, C. A. J. Chem. Soc., Chem. Commun. 1991, 749.
35. For examples of other systems that use edge-on aromatic interactions, see the following. (a) Protein secondary and tertiary structure: Burley, S. K.; Petsko, G. A. Science (Washington, D.C.) 1985, 229, 23. (b) Crystal lattices of aromatic molecules: Desiraju, G. R.; Gavezzotti, A. J. Chem. Soc., Chem. Commun. 1989. 621 and references therein. (c) To effect stereoselectivity in metal complexes: Karpishin, T. B.; Stack, T. D. P.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 6115. (d) In molecular recognition: Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561. Hunter, C. A. J. Chem. Soc., Chem. Commun. 1991, 749.
36. For examples of other systems that use edge-on aromatic interactions, see the following. (a) Protein secondary and tertiary structure: Burley, S. K.; Petsko, G. A. Science (Washington, D.C.) 1985, 229, 23. (b) Crystal lattices of aromatic molecules: Desiraju, G. R.; Gavezzotti, A. J. Chem. Soc., Chem. Commun. 1989. 621 and references therein. (c) To effect stereoselectivity in metal complexes: Karpishin, T. B.; Stack, T. D. P.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 6115. (d) In molecular recognition: Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561. Hunter, C. A. J. Chem. Soc., Chem. Commun. 1991, 749.
37. For examples of other systems that use edge-on aromatic interactions, see the following. (a) Protein secondary and tertiary structure: Burley, S. K.; Petsko, G. A. Science (Washington, D.C.) 1985, 229, 23. (b) Crystal lattices of aromatic molecules: Desiraju, G. R.; Gavezzotti, A. J. Chem. Soc., Chem. Commun. 1989. 621 and references therein. (c) To effect stereoselectivity in metal complexes: Karpishin, T. B.; Stack, T. D. P.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 6115. (d) In molecular recognition: Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561. Hunter, C. A. J. Chem. Soc., Chem. Commun. 1991, 749.
38. The structural properties observed for Cu1(py) and Cu1(lut) appear to be present only in the crystalline state. Preliminary electronic absorbance and circular dichroism results suggest that the complexes racemize upon redissolution at room temperature.